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Novel organic light-emitting compound, application thereof and organic light-emitting device adopting compound

An electroluminescence and compound technology, applied in the field of organic electroluminescence devices, can solve the problems of high driving voltage, low luminous efficiency, low brightness, thermal stability, color purity and device life, and achieve low driving voltage, excellent current and power efficiency. , Improve the effect of driving life

Inactive Publication Date: 2018-05-29
NANJING TOPTO MATERIALS CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The first object of the present invention is to provide a type of organic electroluminescent compound, which has excellent photoelectric performance, and can be applied to organic electroluminescent devices, and can solve the problem of organic electroluminescent devices. High driving voltage, low luminous efficiency, brightness, thermal stability, color purity and device life, etc.

Method used

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  • Novel organic light-emitting compound, application thereof and organic light-emitting device adopting compound
  • Novel organic light-emitting compound, application thereof and organic light-emitting device adopting compound
  • Novel organic light-emitting compound, application thereof and organic light-emitting device adopting compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] The synthesis of embodiment 1 compound 1

[0064] Synthesis of Intermediate-1

[0065] [Reaction 1]

[0066]

[0067] In a dry 3L three-necked flask, add 21.9g (100mmol, 1.0eq.) of N-phenyl-2-naphthylamine and 43.1g (120mmol, 1.2eq.) of 4-bromo-4-iodobiphenyl, then add dry And degassed 1300ml of toluene was used as a solvent, and nitrogen gas was passed for 15 minutes. Then 2.9 g (15% mol) of cuprous iodide, 5.9 g (30% mol) of 1,10-phenanthroline and 63.7 g (300 mol, 3 eq.) of potassium phosphate were added. The temperature was raised to 110°C, and the reaction was carried out for 18 hours. After the reaction was completed, it was cooled to room temperature, suction filtered, the solvent was spun off, and recrystallized with toluene and ethanol to obtain 37.4 g of Intermediate-1 with a yield of 83%.

[0068] Synthesis of Intermediate-2

[0069] [Reaction 2]

[0070]

[0071] In dry 3L there-necked flask, add 16.2g (83mmol, 1.0eq.) Acridone and 37.4g (83mmol,...

Embodiment 2

[0091] The synthesis of embodiment 2 compound 37

[0092] Synthesis of Intermediate-6

[0093] [Reaction 6]

[0094]

[0095] In a dry 3L three-necked flask, add 18.4g (120mmol, 1.2eq.) 4-aminobiphenyl and 24.7g 2-bromodibenzofuran (100mmol, 1.0eq.), then add dry and degassed 900ml toluene As a solvent, nitrogen gas was passed for 15 minutes. Then add 19.2g (200mmol, 2.0eq.) sodium tert-butoxide, 1.8g (2%mol) catalyst Pd2(dba)3 and 8.1ml (4%mol) P(t-bu) 3 Toluene solution (m / v, 10%). The temperature was raised to 100°C, and the reaction was carried out for 6 hours. After the reaction was completed, cool to room temperature, add activated carbon for adsorption, filter with suction, spin off the solvent, and recrystallize with toluene and ethanol to obtain 27.2 g of Intermediate-6 with a yield of 81%.

[0096] Synthesis of Intermediate-7

[0097] [Reaction 7]

[0098]

[0099] Add 18g (81mmol, 1.0eq.) p-iodofluorobenzene and 37.4g (81mmol, 1.0eq.) Intermediate-6 in ...

Embodiment 3

[0127] The synthesis of embodiment 3 compound 54

[0128] Synthesis of Intermediate-13

[0129] [Equation 14]

[0130]

[0131] Add 33g (100mmol, 1.0eq.) m-diiodobenzene and 20.3g (120mmol, 1.2eq.) 3-aminobiphenyl in a dry 3L three-necked flask, then add dry and degassed 1000ml toluene as a solvent, pass Nitrogen for 15 minutes. Then add 19.2g (200mmol, 2.0eq.) sodium tert-butoxide, 1.8g (2%mol) catalyst Pd 2(dba) 3 and 8.1ml (4%mol) P(t-bu) 3 Toluene solution (m / v, 10%). The temperature was raised to 100°C, and the reaction was carried out for 2 hours. After the reaction was cooled to room temperature, activated carbon was added for adsorption, suction filtered, the solvent was spun off, and recrystallized with toluene and ethanol to obtain 31.9 g of Intermediate-13 with a yield of 86%.

[0132] Synthesis of Intermediate-14

[0133] [Equation 15]

[0134]

[0135] Add 31.9g (86mmol, 1.0eq.) of Intermediate-13 and 25.9g (86mmol, 1.0eq.) of 2-bromo-1-fluoro-3-iod...

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PUM

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Abstract

The invention provides a novel organic light-emitting compound, an application thereof and an organic light-emitting device adopting the compound. The compound has a structure shown as follows in thedescription, wherein R1, R2 and R4 are independently C1-C20 linear or branched alkyl, phenyl, pyridyl, naphthyl, phenanthryl, anthryl, phenanthridinyl, biphenyl, pyrimidinyl and triazinyl; R3 is C1-C10 alkyl, or C6-C30 aryl; R5 is hydrogen, deuterium, halogen, C1-C20 linear or branched alkyl, or is selected from a group formed by C6-C30 aryl; R6 and R7 are deuterium, C1-C20 linear or branched alkyl, phenyl, pyridyl, naphthyl, phenanthryl, anthryl, phenanthridinyl, biphenyl, pyrimidinyl and triazinyl; X and Y are C or N respectively, and I is an integer of 0-4, and m and n are 0 or 1. The organic light-emitting compound can be used for preparing the organic light-emitting device, the driving voltage of the device can be reduced, luminous efficiency, brightness, thermal stability, color purity of the device can be improved, and the service life of the device can be prolonged.

Description

technical field [0001] The invention relates to the field of organic electroluminescent materials, in particular to a novel organic electroluminescent compound and an organic electroluminescent device using the organic electroluminescent compound. Background technique [0002] Organic light-emitting devices (Organic Light-emitting Devices, OLED) are spontaneous light-emitting devices using the following principle: when an electric field is applied, fluorescent substances emit light through the recombination of holes injected from the positive electrode and electrons injected from the negative electrode. This self-luminous device has the characteristics of low voltage, high brightness, wide viewing angle, fast response, good temperature adaptability, etc., and has the advantages of being ultra-thin and can be fabricated on flexible panels. It is widely used in mobile phones, tablet computers, TVs, lighting and other fields. [0003] Organic electroluminescent devices have a ...

Claims

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Application Information

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IPC IPC(8): C07D471/10C07D221/20C07D401/12C07D401/04C07D405/04C07D209/86C07D307/91C07D405/12C07D405/10C07F7/08C07C211/55C07C211/58C07C211/61C07C409/14C07C13/72C09K11/06H01L51/50H01L51/54
CPCC09K11/06C07C13/72C07C211/55C07C211/58C07C211/61C07C409/14C07D209/86C07D221/20C07D307/91C07D401/04C07D401/12C07D405/04C07D405/10C07D405/12C07D471/10C07F7/0812C09K2211/1088C09K2211/1092C09K2211/1007C09K2211/1011C09K2211/1029H10K85/622H10K85/625H10K85/626H10K85/615H10K85/6576H10K85/6574H10K85/40H10K85/6572H10K50/15H10K50/16H10K50/17H10K50/18H10K50/11
Inventor 金振禹钱超王晓维聂金龙
Owner NANJING TOPTO MATERIALS CO LTD
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